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240 Main St, Deep River
$599,900
3 Beds ⋅ 2 Baths ⋅ 24200740 MLS
Walking distance to Downtown and a brand new roof! Welcome to 240 Main Street. Full of character and warm appeal, this 3-bedroom, 2-full-bath home offers a unique combination of indoor comfort and a prime outdoor setting. Step inside to discover a beautiful, well-appointed kitchen outfitted with a professional Jade stove-perfect for culinary enthusiasts-with views opening out to a beautifully landscaped, private backyard retreat. Built-ins and original details continue throughout the entire home, while thoughtful updates maximize the use of living space. With lots of flex space in the barn, the first floor hosts amazing space for a gym, second office, hobby room or a billiard room. Upstairs, a private office provides a quiet work-from-home setup. Outdoors, the peaceful, tree-lined yard includes a charming potting shed and abuts a serene church field for maximum privacy. Positioned right across the street from the local park, playground, and baseball fields, you'll enjoy front-row access to community recreation while maintaining your own private oasis. Schedule your private tour today!

240 Main St, Deep River

27 Beechwood Dr, Deep River
$415,000
3 Beds ⋅ 2 Baths ⋅ 24208860 MLS
First time offered in over 50 years! Set on over an acre at the end of a cul-de-sac, this three-bedroom, one-and-a-half-bath home offers a wonderful combination of space, privacy, and potential. Step inside the foyer, where the home opens to two levels of living space. Upstairs, you'll find the main living area along with three bedrooms, including a primary bedroom with its own half bath. The lower level features a spacious family room with a fireplace, providing additional room to relax, entertain, or create a flexible living space. One of the home's standout features is the expansive covered deck spanning the back of the house, overlooking a beautiful backyard with plenty of room to enjoy the outdoors. Additional features include a dedicated laundry room, ample storage, and a one-car garage. Lovingly held by the same seller for more than five decades, this home presents a special opportunity to make it your own and begin its next chapter.

27 Beechwood Dr, Deep River

103 Bushy Hill Rd, Deep River
$769,000
3 Beds ⋅ 3 Baths ⋅ 24208142 MLS
This Stunning, completely remodeled ranch style home is truly move in ready! With an open concept living area, perfect for entertaining or everyday living. There is pleanty of kitchen space with an island, new cabinets & quartz countertops and new appliances, living room area with gas fireplace and dining space. High ceilings and plenty of window to let in the natural light. On one side of the house you have the Master bedroom with two walk-in closets & private master bath. The Laundry room and half bath. On the other side of the house are two additional bedrooms & a full bath. Enjoy the privacy of your back deck accessable from both the living room and master bedroom. The lot is just over two acres, surrounded by private lightly wooded land. With over 1700 sq ft of living space there is still room for expansion over the attached two car garage. With entrances from both the garage or outside, this space has been started for an in-law apartment. Frame work, electric & plumbing have been started. Additional photos will be added soon.

103 Bushy Hill Rd, Deep River

77 Falls Landing Rd, Deep River
$699,900
4 Beds ⋅ 3 Baths ⋅ 24205311 MLS
MAJOR PRICE REDUCTION!! An exceptional opportunity to own over 3,100 square feet w/ waterfront frontage at an incredible value! Offering 4 bedrooms, 2.5 baths & 3,143 square feet of living space, this spacious Colonial is tucked away on a private cul-de-sac overlooking Pratt Read Reservoir w/ approximately 200 feet of waterfront frontage. The home features all-new plumbing, updated bathrooms & a newer HVAC system, with just a few remaining updates offering the next owner an opportunity to add their own style & finishing touches. The spacious eat-in kitchen w/ a large pantry opens to a welcoming family room w/ a gas fireplace, while formal living & dining rooms provide flexible space for entertaining, a home office or den. A dramatic two-story foyer creates an impressive entrance. Upstairs, the primary suite features dual walk-in closets & a spacious bath with a soaking tub & large walk-in shower. The walkout lower level is filled w/ natural light & offers tremendous potential for additional finished living space. Enjoy beautiful water views & recreation right from your backyard-kayak, canoe, fish or simply relax on the oversized deck overlooking the reservoir w/ direct water access. Conveniently located near a popular pick-your-own orchard & just minutes from Valley Regional High School. At $699,900, finding a home with more than 3,000 square feet, waterfront access & this much potential in town is a rare opportunity. Bring your finishing touches & make it yours!!

77 Falls Landing Rd, Deep River

24 Long Hill Rd, Deep River
$519,500
4 Beds ⋅ 2 Baths ⋅ 24205608 MLS
Generous proportions, versatile living spaces and exceptional outdoor amenities define this beautifully appointed four-bedroom, two-bath split-level ranch. The open-concept kitchen, living and dining areas feature hardwood floors, creating an inviting and connected main living space. A fireplace anchors the living room, while the kitchen features stainless steel appliances, including a Sub-Zero refrigerator/freezer. The expansive family room is enhanced by exposed beams and opens directly to a covered patio overlooking the private backyard. Additional rooms provide outstanding flexibility for home offices, a den, fitness room, playroom or other uses. An impressive multi-level deck extends the living space outdoors, offering a beautiful setting for entertaining and relaxing. Set on 1.2 private acres, the property also features a three-car garage with abundant parking and storage. Ideally positioned in an established neighborhood near the Connecticut River, with downtown Deep River and Essex just minutes away, this property offers a wonderful balance of privacy, convenience and quintessential Connecticut River Valley living.

24 Long Hill Rd, Deep River

141 Cedar Swamp Rd, Deep River
$999,900
4 Beds ⋅ 4 Baths ⋅ 24205606 MLS
Set on nearly six beautifully landscaped acres, this distinctive four-bedroom, three-and-a-half-bath estate blends timeless character with thoughtfully designed living spaces. A welcoming foyer with brick flooring sets the tone, with custom details throughout including wide-board floors, exposed beams, french doors, detailed millwork and four fireplaces. The kitchen is anchored by an impressive oversized fireplace spanning nearly an entire wall, fitted with a gas insert, and a large center island that creates a natural gathering place. The expansive great room features soaring ceilings, custom windows, built-ins, beautiful woodwork and a fireplace, with french doors opening to a covered rear porch overlooking the grounds. The private primary suite encompasses the entire third floor, creating a true retreat. Beyond the home, stone patios and walls create inviting spaces around the saltwater inground pool and pool house. A professionally engineered pond offers swimming and fishing in warmer months and skating in winter. A substantial barn, additional two-car barn/garage and mature landscaping complete this exceptional private estate.

141 Cedar Swamp Rd, Deep River

58 Union St, Deep River
$429,900
2 Beds ⋅ 1 Baths ⋅ 24179608 MLS
Welcome to 58 Union Street in the heart of charming Deep River! Just moments from the vibrant downtown, this beautifully updated home offers the perfect blend of character, comfort, and modern efficiency. Inside, you'll find hardwood floors, timeless architectural charm, and a thoughtfully renovated interior featuring a remodeled kitchen with all-new stainless-steel appliances, an updated bathroom with new fixtures, plumbing and a newly created first-floor laundry room converted from the former utility space for added convenience. The electric was upgraded to 200 amps & new energy-efficient mini-split systems provide year-round heating and cooling, while solar panels help keep utility costs low. Step outside to enjoy the newly installed backyard patio-an inviting space for relaxing or entertaining. Garden enthusiasts will appreciate the unique outdoor sink with both hot and cold water, making gardening projects and outdoor cleanup easier than ever. Located just a short stroll from the center of town, you'll love the convenience of Deep River's charming shops, restaurants, parks, and community events. Experience the best of small-town living, including the nationally recognized annual Deep River Ancient Muster, one of the area's most celebrated traditions. This move-in-ready home is the perfect opportunity to enjoy comfort, efficiency, and an unbeatable in-town location. A great condo alternative or second home.

58 Union St, Deep River

170 Bushy Hill Rd, Deep River
$850,000
3 Beds ⋅ 4 Baths ⋅ 24192283 MLS
Modern style abounds in this 3-bedroom, 2 full bath, 2 half bath home offering exceptional flexibility, character, and entertaining space. The open-concept main level features vaulted ceilings, dramatic architectural lines, and seamless flow between the kitchen, dining, and living areas. A striking firebox anchors the living room, while the four-season sunroom opens through French doors to a private tiered deck complete with a custom stone fireplace-perfect for outdoor gatherings year-round. The second floor offers two bedrooms plus a spacious primary suite with cathedral ceilings and a truly one-of-a-kind spa bath inspired by a traditional retreat, featuring custom tilework and natural stone accents for a serene, luxurious experience. The finished lower level includes a recreation room and custom-designed bar, creating the ideal space for entertaining. A two-car garage is complemented by a third attached bay leading to a professional woodworking shop with French door access to the beautifully landscaped backyard. Set on picturesque grounds with a gentle stream along the eastern boundary, the property also features mature fruit trees and a productive vegetable garden. Whether you're an entertainer, hobbyist, home-based business owner, or seeking potential in-law living space, this unique property offers endless possibilities and versatile living in a truly special setting.

170 Bushy Hill Rd, Deep River

87 Main St, Deep River
$1,150,000
8 Beds ⋅ 6 Baths ⋅ 24193614 MLS
VC Property Group is proud to present a rare two-parcel assemblage in Deep River, Connecticut, featuring a newer construction single-family residence, a five-unit mixed-use building with four residential apartments and one retail unit, and a contiguous 0.30-acre vacant parcel. Located in the highly desirable Lower Connecticut River Valley, the property is just 0.4 miles from Downtown Deep River and approximately 1 mile from Downtown Chester, providing convenient access to acclaimed restaurants, boutique shopping, marinas, and the region's historic village centers. Deep River continues to benefit from strong residential demand driven by limited housing inventory and spillover from neighboring Chester and Essex. The assemblage offers immediate cash flow with meaningful long-term upside, including the potential for a municipal lot line adjustment to combine the vacant parcel with the single-family residence, creating a premium residential asset, or to retain the parcel for future single-family development. Combining stabilized income, intrinsic residential value, and embedded development optionality, this offering presents a compelling investment opportunity in one of Connecticut's most desirable river communities.

87 Main St, Deep River

106 Meadow Woods Rd, Deep River
$1,065,000
3 Beds ⋅ 2 Baths ⋅ 24192002 MLS
Essex Village is a short walk to this one-of-a-kind home, privately set on over three picturesque acres. Just moments from the Essex town line, this extraordinary custom home is the result of an exceptional architectural transformation, blending timeless New England character with thoughtful, high-end design. Enjoy a peaceful, private setting while being just minutes from the charming village centers of Deep River and Essex, with their acclaimed restaurants, boutique shops, marinas, yacht clubs, the Connecticut River Museum, and the historic Griswold Inn. A comprehensive redesign of the home's exterior was completed by renowned architect Christopher Arelt, featuring all-new windows, structural insulated panels for enhanced energy efficiency, cedar shingle siding, copper gutters, Azek trim, a 4-zone heating system, an expansive Ipe deck and stairs, a bluestone patio, and a private outdoor shower. A brand-new well, drilled in May, and a whole-house generator powered by a 500-gallon underground propane tank provide year-round comfort and peace of mind. The home's showpiece is the spectacular four-season sunroom. This breathtaking space features a coffered beadboard ceiling, rich Brazilian cherry flooring, walls of windows, a wood-burning stove, custom built-in seating, and French doors opening onto the expansive Ipe deck, creating an extraordinary setting for year-round living and entertaining.

106 Meadow Woods Rd, Deep River

391 Main St Unit 134, Deep River
$205,000
1 Beds ⋅ 1 Baths ⋅ 24192095 MLS ⋅ Georgetown Woods BLDG.
Welcome to one of Deep River's hidden treasures! Ideally located in the heart of the beautiful Connecticut River Valley, this inviting condominium with low monthly HOA of $272 offers comfortable, low-maintenance living in a well-maintained 50-unit community with easy access to Routes 9 and I-95.Enjoy the convenience of nearby Main Street, where you'll find a grocery store, liquor store, charming shops, restaurants, marinas, and yacht clubs just minutes away. Freshly painted throughout, this upper level ranch unit is light-filled and features recently replaced living room flooring, a new stainless refrigerator, oven/range, and attractive new carpeting in the bedroom, making it truly move-in ready. The laundry and storage area are located on the lower level. The property includes one assigned parking space plus ample visitor parking. The HOA covers trash removal, lawn maintenance, and snow removal, allowing you to enjoy carefree living year-round. Whether you're looking for a full-time residence, a weekend getaway, or an investment in one of Connecticut's most picturesque Connecticut River towns, this condo is an outstanding opportunity. Complex borders Canfield Woods Nature Preserve with walking trails. Just a few miles from the historic villages of Essex and Old Saybrook, you will enjoy easy access to boating, beaches, dining, shopping, and all the charm of the Connecticut shoreline. You'll love calling Deep River home!

391 Main St Unit 134, Deep River

163-165 Main St, Deep River
$795,000
6 Beds ⋅ 3 Baths ⋅ 24178835 MLS
This five unit mixed-use opportunity is located in the quintessential downtown of Deep River, CT. The downtown corridor of this rural river community provides walkable access to a variety of goods and services including health care, grocery, hardware, restaurants, and cafes. Both commercial anchor tenants at this location have leases in place through 2030 that increase annually in accordance with the Consumer Pricing Index (CPI). All three residential units are on annual leases including (2) 1 bedroom units and (1) 2 bedroom unit. On street parking for customers and tenants. The third floor space was originally a Masonic Lodge and is currently used as storage. The space is about 1,200 square feet and recent zoning changes now allow it to be converted into at least one additional unit. Both the fire marshal and building inspector came out to assess the building and indicated that the turn time to review a proposed site plan would be 2-4 weeks. Buyer to perform all due diligence.

163-165 Main St, Deep River

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